1-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid → 6-[2-(4-Chloro-phenyl)-2H-pyrazol-3-yl]-1-(2,4-difluoro-phenyl)-1H-benzoimidazole

HRID 2202468Notes

Reaction equation

HRID 2202468 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])[C:6]=2[CH:18]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30](B(O)O)=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:30]([C:2]3[CH:3]=[CH:4][C:5]4[N:9]=[CH:8][N:7]([C:10]5[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=5[F:17])[C:6]=4[CH:18]=3)=[CH:29][CH:28]=[N:27]2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 900951261-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid2×HCID 900954196-bromo-1-(2,4-difluoro-phenyl)-1H-benzo[d]imidazole2×

Product 1

HCID 736736716-[2-(4-Chloro-phenyl)-2H-pyrazol-3-yl]-1-(2,4-difluoro-phenyl)-1H-benzoimidazole

Procedure

The title compound, off-white solid (29 mg, 22%), MS (ISP) m/z=407.4 [(M+H)+], mp 133° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-(2,4-difluoro-phenyl)-1H-benzo[d]imidazole (intermediate K) (100 mg, 324 μmol) and 1-(4-chloro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate D) (79.2 mg, 356 μmol).

Sources & evidence

ORD record
ord-8bc3fe62b32d4b25a87f53af5eeb8aea
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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